Isopropyl iodide → 2-Bromo-4-nitro-1-[(propan-2-yl)oxy]benzene

HRID 1420691Notes

Reaction equation

HRID 1420691 reaction equation
I[CH:2]([CH3:4])[CH3:3].[Br:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[OH:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:2]([O:15][C:7]1[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=1[Br:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 221092-Bromo-4-nitrophenol

Product 1

HCID 187825712-Bromo-4-nitro-1-[(propan-2-yl)oxy]benzeneYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Iodopropane (2.2 g) was added to a mixture of 2-bromo-4-nitrophenol (2.5 g) and potassium carbonate (5 g) in acetone (30 ml) and the mixture heated under reflux for 18 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography, eluting with hexane/EtOAc (90:10), to give the title compound (2.8 g, 94%); δH (250MHz, CDCl3) 1.42 (6H, d, J 5.7Hz, OCH(CH3)2), 4.75 (1H, m, OCH(CH3)2), 6.93 (1H, m, ArH), 8.20 (1H, m, ArH), 8.46 (1H, s, ArH).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was evaporated under reduced pressure
  5. additionWater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated under reduced pressure
  10. customThe residue was purified by flash chromatography
  11. washeluting with hexane/EtOAc (90:10)

Sources & evidence

ORD record
ord-4e68f1bffda14a7cb4c98afd65ba0ef6
Source dataset
uspto-grants-2000_06
Patent number
US06071928

Reaction notes

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